Cyanuric chloride → tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13](=O)[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]#[N:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title product of Example 10 (10.81 g, 50.45 mmol) and cyanuric chloride (5.58 g, 30.3 mmol) was stirred in DMF (30 mL) for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were washed with aq. sodium carbonate, water, brine dried over sodium sulphate, filtered and concentrated to afford the title product (8.34 g, 84%) as a colourless oil.
Workup
- customThe reaction mixture was partitioned between ethyl acetate and water
- washThe organic extracts were washed with aq. sodium carbonate, water, brine
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bc86d84ef4504911a8a7d9963b65b34e
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678796B2
Reaction notes
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